Hester was raised by his mother and stepfather. He lived on the Channel Island of
Sark from the age of four, and was educated at
Elizabeth College in
Guernsey. His biological father is the actor
Tony Smee. Aged 19 he applied for a job with horses in the
UK at
The Fortune Centre of Riding Therapy and on the centre's
skewbald mare, Jolly Dolly, he won the 1985 Young Dressage Rider Championship. Moving to
Bourton-on-the-Hill he competed at the first
Blenheim Horse Trials and won the Spillers Dressage with Jumping Championship. He next rode for Dr Wilfried Bechtolsheimer ==2011 European Dressage Championship==